O-Phenylenediamine → HCID 9909614, compound

HRID 375527Notes

Reaction equation

HRID 375527 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[C:9]1([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=3)[CH2:17][CH2:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>[N+](C1C=CC=CC=1)([O-])=O>[NH3:1].[C:9]1([N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:32]=[CH:31][C:28]([C:29]4[NH:8][C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[N:1]=4)=[CH:27][CH:26]=3)[CH2:19][CH2:20]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7243O-PhenylenediamineHCID 55234Benzaldehyde, 4-(3-(4-phenyl-1-piperazinyl)propoxy)-

Product 2

HCID 222AmmoniaHCID 9909614HCID 9909614, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1,2-diaminobenzene (0.67 g) and 4-[3-(4-phenylpiperazin-1-yl)propoxy]benzaldehyde (Example A) (2.00 g) in nitrobenzene (65 mL) is stirred for 16 hours at 160° C. The solvent is distilled off under high vacuum and the resulting solid is purified by medium pressure liquid chromatography (MPLC) on silica gel eluting with 200:8:1 dichloromethane: ethanol:0.880 aqueous ammonia to give 0.97 g of the title compound as a tan solid; mp 240°-244° C.

Workup

  1. distillationThe solvent is distilled off under high vacuum
  2. customthe resulting solid is purified by medium pressure liquid chromatography (MPLC) on silica gel eluting with 200:8:1 dichloromethane

Sources & evidence

ORD record
ord-e796f27f381b48369ecc4b083c90b0cf
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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